An organic compound and use thereof

Abstract

The present application relates to an organic compound, and also relates to an organic electroluminescent device using the same. The organic compound of the present application has a structure as shown in formula (1), formula (2) or formula (3). The compound of the present application has multiple resonance effects, and has the characteristics of high luminescent efficiency, narrow light spectrum emission and high stability. The organic electroluminescent device using the compound of the present application has higher external quantum efficiency and longer device life.

Description

Technical Field

[0001] This invention relates to an organic compound, and more particularly to a compound that can be used in organic electroluminescent devices, and also to organic electroluminescent devices employing the organic compound. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, meet, and recombine within the organic layer to emit light. Due to their advantages such as high brightness, fast response, wide viewing angle, simple manufacturing process, and flexibility, OLED devices have attracted significant attention in the fields of new display technology and new lighting technology. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and its application is expected to expand further into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] As OLED technology continues to advance in both lighting and display fields, research into its core materials is receiving increasing attention. This is because a high-efficiency, long-lifespan OLED device is typically the result of optimized device structure and the combination of various organic materials. To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve OLED device performance, innovation in OLED device structure and manufacturing processes is necessary, along with ongoing research and innovation in the optoelectronic functional materials used in OLED devices to develop higher-performance functional materials. Based on this, the OLED materials community has been dedicated to developing new organic electroluminescent materials to achieve devices with low start-up voltages, high luminous efficiency, and superior lifespans.

[0004] In the selection of OLED light-emitting materials, singlet-state luminescent fluorescent materials have good lifetimes and low prices, but low efficiency; triplet-state luminescent phosphorescent materials have high efficiency, but are expensive, and the lifetime problem of blue light-emitting materials has not yet been solved. Adachi of Kyushu University in Japan proposed a new class of organic light-emitting materials, namely thermally activated delayed fluorescence (TADF) materials. This type of material utilizes donor-acceptor separation to obtain a smaller singlet-triplet bandgap (ΔE). ST (<0.3eV), thus enabling triplet excitons to be converted into singlet excitons for emission via reverse intersystem crossing (RISC), thereby achieving an internal quantum efficiency of 100%.

[0005] TADF materials can theoretically achieve 100% internal quantum efficiency through the upconversion process from triplet to singlet states, thus enabling highly efficient luminescence. Traditional TADF molecules have a highly twisted electron donor-acceptor structure, which cannot simultaneously accommodate high reverse intersystem crossing rates and high radiative transition rates, limiting further efficiency improvements. Furthermore, because TADF materials emit light in the CT state, their broad spectrum cannot meet the color requirements of BT.2020, thus restricting their further application in the display field. Boron-nitrogen-based multiple resonance MR-TADF materials, however, possess advantages such as high color purity and high luminous efficiency, attracting widespread attention from the scientific and industrial communities. However, because the peripheral substituents have little effect on the S1 level, it is difficult to control the material's emission color, limiting it to the blue-deep blue region. Moreover, the significant overlap between its HOMO and LUMO levels restricts ΔE... ST The relatively large size and slow reverse intersystem crossing rate greatly limit the further application of MR-TADF materials in high-resolution displays, full-color displays, and white light illumination. Summary of the Invention

[0006] In one aspect, the present invention provides an organic compound having a structure as shown in formula (1), formula (2) or formula (3):

[0007]

[0008] in:

[0009] Cycles Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently selected from aromatic rings of C6 to C60 or heteroaromatic rings of C3 to C60;

[0010] W1 and W2 are independently C-C single bonds, O, S, Se, NR7, CR8R9, or SiR, respectively. 10 R 11 m1 and m2 are each independently 0 or 1;

[0011] W3 and W4 are each independently selected from N or C;

[0012] Y is selected from O, S, Se, NR 12 CR 13 R 14 or SiR 15 R 16 ;

[0013] X is selected from BAr6 (R6) n6C=O, or X is selected from substituted or unsubstituted fluorenyl groups, wherein when the fluorenyl group has a substituent, the substituent is selected from one of C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0014] The ring Ar6 is selected from aromatic rings of C6 to C60 or heteroaromatic rings of C3 to C60;

[0015] R1, R2, R3, R4, R5 and R6 are each independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0016] n1, n2, n3, n4, n5, and n6 are each independently selected from integers from 1 to 10;

[0017] When n1, n2, n3, n4, n5, and n6 are each independent integers greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, multiple R4s, multiple R5s, and multiple R6s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, the multiple R4s are either not connected or connected in a cycle, the multiple R5s are either not connected or connected in a cycle, and the multiple R6s are either not connected or connected in a cycle.

[0018] R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 and R 16 Each group is independently selected from one of the following groups, either substituted or unsubstituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl; and R8 and R9 are either not connected or connected to form a ring, R 10 With R 11 The elements are either not connected or connected in a loop, R 13 With R14 The elements are either not connected or connected in a loop, R 15 With R 16 They are either not connected or connected in a loop;

[0019] And R 12 R 13 R 14 R 15 R 16 Each of them is independent and either not connected to rings Ar2 and Ar5, or connected to form a ring. 12 R 13 R 14 R 15 R 16 Each of them is independent and not connected to R2 or R5, or connected to form a loop; and each of them is independent and not connected to ring Ar4 or ring Ar5, or connected to form a loop.

[0020] When the above R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 and R 16 When each of the above substituents is present independently, each substituent is independently selected from one or a combination of two of the following: halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C6-C30 aryl, substituted or unsubstituted C6-C60 arylboryl, and C3-C30 heteroaryl.

[0021] Preferably, each of the rings Ar1, Ar2, Ar3, and Ar4 independently has the structure shown in formula (a) or formula (b), and the double bonds indicated by the dashed lines represent the fusion positions of the groups:

[0022]

[0023] In equation (a), Z 1 Z 2 Z 3 Z 4 Each is independently selected from C, CH, or N;

[0024] In equation (b), Z 5The components are selected from O, S, NR1, or CR2R3, wherein R1, R2, and R3 are each independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl. When substituents are independently present on R1, R2, and R3, each substituent is independently selected from one of halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0025] The ring H is selected from one of the C6-C30 aromatic rings and the C3-C30 heteroaromatic rings.

[0026] More preferably, ring H is a benzene ring; Z 5 Selected from S, NR1, or CR2R3.

[0027] More preferably, one of the rings Ar1, Ar2, Ar3, and Ar4 is the structure shown in formula (b), and the other ring structures are each independently the structure shown in formula (a).

[0028] Furthermore, each of the rings r1, Ar2, Ar3, Ar4, Ar5, and Ar6 is independently selected from aromatic rings of C6 to C30 or heteroaromatic rings of C3 to C30.

[0029] Preferably, rings Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of benzene ring, naphthyl ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indole-carbazole, benzothiophene, dibenzothiophene, and thiophene; preferably, rings Ar5 and Ar6 are each independently selected from phenyl, naphthyl, anthraceneyl, benzoanthracene, phenanthrene, pyrene, pyrene, peryl, fluoranthracene, tetraphenyl, pentaphenyl, benzopyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophene, and benzothiophene. One of the following: phenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoyl, indoxarcarbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indoxolyl, imidazoyl, benzimidazolyl, naphthiazoleyl, phenanthridineimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxolinimidazolyl, oxazolyl, benzooxazolyl, naphthiazoleyl, anthraquinoxazolyl, phenanthridineimidazolyl, 1,2-thiazoyl, 1,3-thiazoyl, benzothiazoyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxolinyl;

[0030] More preferably, each of the rings Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is independently selected from one of the following: benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, or thiophene; most preferably, each of the rings Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is independently a benzene ring.

[0031] More preferably, in formula (1), W1 and W2 are independently CC single bonds, S, Se, NR7, and CR8R9, respectively; m1 and m2 are 1; in formula (2), W1 is independently CC single bonds, S, Se, NR7, and CR8R9, respectively; m1 and m2 are 1; preferably, in formula (1), W1 and W2 are independently CC single bonds, S, NR7, and CR8R9, respectively; m1 and m2 are 1; in formula (2), W1 is independently CC single bonds, S, NR7, and CR8R9, respectively; m1 and m2 are 1; more preferably, in formula (1), W1 and W2 are CC single bonds; m1 and m2 are 1; in formula (2), W1 is a CC single bond; m1 and m2 are 1.

[0032] Furthermore, in the compound formulas (1), (2), and (3) of the present invention, when X is BAr6 (R6)... n6 When Y is selected from O, S, Se, NR 12 CR 13 R 14 or SiR15 R 16 Preferably, when X is BAr6(R6)... n6 When Y is selected from O, S, NR 12 CR 13 R 14 The most preferred scenario is when X is BAr6(R6). n6 When Y is selected from O, S, NR 12 ;

[0033] When X is C=0, Y is selected from O, S, Se, NR. 12 CR 13 R 14 or SiR 15 R 16 Preferably, when X is C=0, Y is selected from O, S, and NR. 12 CR 13 R 14 Most preferably, when X is C=0, Y is selected from O, S, and NR. 12 ;

[0034] When X is a substituted or unsubstituted fluorene group, Y is selected from O, S, Se, and NR. 12 CR 13 R 14 or SiR 15 R 16 Preferably, when X is a substituted or unsubstituted fluorene group, Y is selected from O, S, and NR. 12 CR 13 R 14 Most preferably, when X is a substituted or unsubstituted fluorene group, Y is selected from O, S, and NR. 12 .

[0035] More preferably, n1, n2, n3, n4, n5 and n6 are each independently selected from integers from 1 to 5;

[0036] R1, R2, R3, R4, R5, and R6 are each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, halogen, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indeno[a]fluorenyl, triphenyl Polyindyl, isotrimericindyl, spirotrimericindyl, spiroisotrimericindyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indoxarcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthreneazoleyl, pyridinazoleyl, pyrazinazoleyl, quinoxalinazoleyl, oxazolyl, benzooxazolyl Naphthooxazolyl, anthrazooxazolyl, phenanthreneoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2 One of the following: 3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridyl, indazinyl, benzothiadiazolyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, and di(2,4,6-triisopropylphenyl)boryl;

[0037] More preferably, R1, R2, R3, R4, R5, and R6 are each independently selected from the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indofluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrroleyl, isoyindolyl, One of the following groups: carbazolyl, indocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinel, phenanthridinel, pyrazolyl, indazolel, imidazolyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups;

[0038] Most preferably, R1, R2, R3, R4, R5 and R6 are each independently selected from the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, carbazolyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of two of the above groups.

[0039] More preferably, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirophenyl Difluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthizimidazoleyl, phenanthridine Imidazolyl, pyrazinimizolyl, quinoxalinimizolyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1, 2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, indazyl, benzothiadiazolyl, or a combination thereof;

[0040] Preferably, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrroleyl, isoyindolyl, carbazoleyl, indocarbazoleyl, pyridine One of the following groups: yl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination thereof;

[0041] Most preferably, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 Each of the following substituents is independently selected from one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyano, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, or a combination of two of the above groups.

[0042] It should be noted that, unless otherwise defined below, all technical and scientific terms used herein are intended to have the same meaning as commonly understood by those skilled in the art. References to technical terms herein refer to techniques commonly understood in the art, including variations or equivalent substitutions of techniques that are obvious to those skilled in the art. While it is believed that the following terms will be well understood by those skilled in the art, the following definitions are set forth to better explain the invention.

[0043] In this specification, the expression Ca to Cb indicates that the group has a to b carbon atoms. Unless otherwise specified, this number of carbon atoms generally does not include the number of carbon atoms in the substituents. When describing C1 to C30, it includes, but is not limited to, C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc. Other numerical ranges are not elaborated.

[0044] The terms “including,” “comprising,” “having,” “containing,” or “involving,” and their other variations herein, are inclusive or open-ended and do not exclude other unlisted elements or method steps.

[0045] In this invention, unless otherwise specified, the description of chemical elements generally includes the concept of isotopes with the same chemical properties. For example, the description of "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes... 12 C 13 C, etc., will not be elaborated further.

[0046] In this invention, heteroatoms are generally selected from N, O, S, P, Si and Se, and are preferably selected from N, O and S.

[0047] As used herein, the terms “heterocyclic group” and “heterocycle” refer to a saturated (i.e., heterocyclic alkyl) or partially unsaturated (i.e., having one or more double and / or triple bonds within the ring) cyclic group having at least one ring atom selected from N, O and S and the remaining ring atoms being C.

[0048] As used herein, the terms “(aryl)aryl” and “aromatic ring” refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π-electron system. As used herein, the terms “(heteroaryl)aryl” and “heteroaromatic ring” refer to monocyclic, bicyclic, or tricyclic aromatic ring systems. As used herein, the term “aralkyl” preferably means an aryl or heteroaryl-substituted alkyl group, wherein the aryl, heteroaryl, and alkyl groups are as defined herein.

[0049] As used herein, the term “halogenated” or “halogenated” is defined as including F, Cl, Br, or I.

[0050] The term "substitution" refers to the selective replacement of one or more (e.g., one, two, three, or four) hydrogen atoms on a specified atom by a designated group, provided that the substitution does not exceed the normal valence of the specified atom in the present case and that the substitution forms a stable compound. Combinations of substituents and / or variables are permitted only if such combinations form a stable compound.

[0051] If a substituent is described as being “independently selected” from a group, then each substituent is selected independently of the others. Therefore, each substituent may be the same as or different from another (other) substituent.

[0052] As used herein, the term "one or more" means one or more under reasonable conditions, such as two, three, four, five, or ten.

[0053] Unless otherwise specified, as used herein, the connection point of a substituent may be derived from any suitable location of the substituent.

[0054] When the bond of a substituent is such that it passes through the ring and connects two atoms, then such a substituent can be bonded to any cyclic atom in the substituted ring.

[0055] The term “about” means within ±10% of the stated value, preferably within ±5%, and more preferably within ±2%.

[0056] In the structural formulas disclosed in this specification, the way the ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0057] Unless otherwise specified, the C6-C60 aromatic rings and C3-C60 heteroaromatic rings mentioned above in this invention refer to aromatic groups that satisfy the π-conjugated system, including both monocyclic residues and fused-ring residues. A monocyclic residue refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, diphenyl, and terphenyl. A fused-ring residue refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused together by sharing a ring edge, such as naphthyl, anthracene, and phenanthrene. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are independent of each other and connected by a single bond, such as pyridine, furan, and thiophene. A fused-ring heteroaryl group refers to a molecule formed by the fusion of at least one phenyl group and at least one heteroaryl group, or by the fusion of at least two heteroaryl rings, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, and dibenzothiophene.

[0058] In this specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, more preferably an aromatic ring from the group consisting of phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimenyl, isotriinyl, spirotriinyl, and spiroisotriinyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracene group is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene group is selected from 1-pyrene, 2-pyrene, and 4-pyrene; and the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl. Preferred examples of aromatic rings in this invention include those composed of phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indene, fluorenyl and their derivatives, fluoranyl, triphenylene, pyrene, perylene, etc. The group is selected from the group consisting of 1-triphenyl-4-yl, 3-triphenyl-3-yl, 2-triphenyl-2-yl, 4-triphenyl-3-yl, 3-triphenyl-4-yl, 3-triphenyl-3-yl, and 3-triphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracene group is selected from the group consisting of 1-anthrayl, 2-anthrayl, and 9-anthrayl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorenyl, 9,9-spirodifluorenyl, and benzo[a]fluorenyl; the pyrene group is selected from the group consisting of 1-pyrene, 2-pyrene, and 4-pyrene; and the tetraphenyl group is selected from the group consisting of 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl.

[0059] In this specification, the substituted or unsubstituted C6-C60 aryl group is preferably a C6-C30 aryl group, more preferably a group from the group consisting of phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimenyl, isotriinyl, spirotriinyl, and spiroisotriinyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracene group is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene group is selected from 1-pyrene, 2-pyrene, and 4-pyrene; and the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl. Preferred examples of aryl groups in this invention include those composed of phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indene, fluorenyl and their derivatives, fluoranyl, triphenylene, pyrene, perylene, etc. The group is selected from the group consisting of 1-triphenyl-4-yl, 3-triphenyl-3-yl, 2-triphenyl-2-yl, 4-triphenyl-3-yl, 3-triphenyl-4-yl, 3-triphenyl-3-yl, and 3-triphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracene group is selected from the group consisting of 1-anthrayl, 2-anthrayl, and 9-anthrayl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorenyl, 9,9-spirodifluorenyl, and benzo[a]fluorenyl; the pyrene group is selected from the group consisting of 1-pyrene, 2-pyrene, and 4-pyrene; the tetraphenyl group is selected from the group consisting of 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl. The C6-C60 aryl groups of this invention can also be groups formed by single-bonded or / and fused combinations of the above groups.

[0060] In this specification, the substituted or unsubstituted C3-C60 heteroaryl ring is preferably a C3-C30 heteroaryl ring, which can be a nitrogen-containing heteroaryl, an oxygen-containing heteroaryl, a sulfur-containing heteroaryl, etc. Specific examples include: furanyl, thiopheneyl, pyrroleyl, pyridyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl Benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenanthiazinyl, phenanthiazinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthoimidazoleyl, phenanthromidazolyl, pyridiniumimidazolyl, quinoxoliniumimidazolyl, oxazolyl, benzooxazolyl, naphthooxazolyl, anthraquinonexazolyl, phenanthromidazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl Benzopyrimidinyl, quinoxalinyl, 1,5-diazatharthryl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetrazapyrene, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1, Heteroaromatic rings formed by 2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purine, pteridine, indazinyl, benzothiadiazole, etc. As a preferred example of the heteroaromatic ring in this invention, it is a heteroaromatic ring of furanyl, thiopheneyl, pyrroleyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives, wherein the carbazoleyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole or indolocarbazole.

[0061] In this specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furanyl, thiopheneyl, pyrroleyl, pyridyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives, quinolinyl, isoquinolinyl, acridineyl, phenanthridine Benzyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenanthiazinyl, phenazinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthiazoleyl, pyridinium-imidazolyl, pyrazinium-imidazolyl, quinoxalinium-imidazolyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoneium-oxazolyl, phenanthoxoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl Pyridyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl Azolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purine, pteridine, indazinyl, benzothiadiazole, etc. Preferred examples of heteroaryl groups in this invention include furanyl, thiopheneyl, pyrroleyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, and their derivatives. The carbazoleyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole. The C3-C60 heteroaryl groups of this invention can also be groups formed by single-bonded or / and fused combinations of the above groups.

[0062] In this specification, the term "chain alkyl" includes both straight-chain and branched alkyl groups. Examples of C1-C20 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl-neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc. Examples of C1-C20 chain haloalkyl groups include: trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, etc.

[0063] In this specification, C3-C20 cycloalkyl groups include monocycloalkyl and polycycloalkyl groups, and specific examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc.

[0064] In this specification, alkoxy refers to a group composed of the above-mentioned chain alkyl group and oxygen, or a group composed of the above-mentioned cycloalkyl group and oxygen.

[0065] Examples of C1 to C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and isopentoxy are preferred, and methoxy is more preferred.

[0066] In this specification, examples of C1-C20 silanes can be silanes substituted with groups listed in the C1-C20 silanes, i.e., groups formed by substituting one, two, or three hydrogens on a silane with the aforementioned chain alkyl or cycloalkyl groups. Specific examples include: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, and other such groups.

[0067] Furthermore, the compounds of general formula (1) of the present invention may preferably be compounds with the following specific structures: A-1 to A-200, B-1 to B-200, C-1 to C-168, these compounds are only representative:

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] The structural design innovation of this invention lies in increasing the degree of conjugation of the molecule by introducing a six-membered ring below the central benzene ring in the parent structure. On one hand, introducing the six-membered ring increases the degree of conjugation, reduces the emission band gap, and thus causes a redshift in light color. Furthermore, by altering the electron-withdrawing and electron-donating abilities of X and Y on the six-membered ring, the emission color can be broadly adjusted, achieving a wider color gamut coverage. On the other hand, increasing the degree of conjugation through a six-membered ring also significantly improves the structural rigidity of the molecule, thereby reducing the relaxation degree of the excited state structure and improving the luminescence efficiency, color purity, and stability of the molecule.

[0093] When X is an electron-withdrawing group, such as microboron or carbonyl, it can lower the LUMO energy level, significantly reducing the emission band gap and redshifting the emission, thereby achieving narrow-spectrum green or even orange-red light emission. Furthermore, when X is microboron or fluorene, its distorted structure can effectively reduce intermolecular interactions, thereby reducing problems such as redshift, broadening, and efficiency reduction caused by molecular stacking. It can also significantly suppress concentration quenching effects, improve device stability and reproducibility, and increase doping concentration, thereby reducing the difficulty of device fabrication and facilitating the commercial application of the material.

[0094] When Y is an electron-donating group such as O, S, or Se, it can increase the HOMO energy level, thereby reducing the emission band gap and resulting in a redshift in emission. Furthermore, S and Se are heavy atoms, which can promote spin-orbit coupling through the heavy atom effect, thus facilitating the upconversion of triplet excitons and improving luminescence efficiency and device stability. However, when Y is an NR... 12 CR 13 R 14 or SiR 15 R 16 When electron-donating groups are used, not only can the light color be red-shifted, but the R group can also be a sterically hindered group, which can effectively reduce the interaction between molecules. This reduces problems such as red-shift, broadening, and efficiency reduction caused by molecular stacking, significantly suppresses the concentration quenching effect, improves the stability and repeatability of the device, and can also increase the doping concentration to reduce the fabrication difficulty of the device, which is conducive to the commercial application of the material.

[0095] Meanwhile, because the target molecule designed in this invention has a significantly narrower half-width (13-20 nm) compared to boron nitrogen dye molecules in the prior art, it has a longer lifetime when prepared in organic optoelectronic devices.

[0096] In addition, the preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are readily available, and it is suitable for mass production scale-up.

[0097] A second aspect of the invention also protects the application of any of the compounds shown in the above general formula as functional materials in organic electronic devices, including: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper, preferably organic electroluminescent devices.

[0098] Thirdly, the present invention also provides an organic electroluminescent device, including a substrate, including a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer contains a compound represented by any of the above general formulas (1), (1-1) to (1-3).

[0099] Specifically, one embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains the general formula compound of the present invention shown above.

[0100] OLED devices prepared using the compounds of this invention have low start-up voltage, high luminous efficiency, and better lifespan, which can meet the current requirements of panel manufacturers for high-performance materials. Detailed Implementation

[0101] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0102] All the chemical reagents used in this invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, and potassium carbonate, were purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0103] The synthesis method of the compounds of the present invention will be briefly described below.

[0104] Synthesis Examples

[0105] Representative synthetic pathways:

[0106]

[0107] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0108] Synthesis Examples

[0109] Synthesis Example 1:

[0110] Synthesis of compound A-1

[0111]

[0112] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-1-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-1 (28% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 711.30; elemental analysis results: theoretical values: C, 86.10; H, 4.96; B, 3.04; N, 5.91; experimental values: C, 86.11; H, 4.96; B, 3.05; N, 5.91.

[0113] Synthesis Example 2:

[0114] Synthesis of compound A-4

[0115]

[0116] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-4-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-4 (31% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 935.55; elemental analysis results: theoretical values: C, 85.98; H, 7.22; B, 2.31; N, 4.49; experimental values: C, 85.98; H, 7.23; B, 2.31; N, 4.51.

[0117] Synthesis Example 3:

[0118] Synthesis of compound A-7

[0119]

[0120] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-7-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-7 (30% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1041.42; elemental analysis results: theoretical values: C, 86.46; H, 4.74; B, 2.08; N, 6.72; experimental values: C, 86.46; H, 4.75; B, 2.08; N, 6.72.

[0121] Synthesis Example 4:

[0122] Synthesis of compound A-19

[0123]

[0124] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-19-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-19 (24% yield, HPLC purity 98%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1041.42; elemental analysis results: theoretical values: C, 86.46; H, 4.74; B, 2.08; N, 6.72; experimental values: C, 86.46; H, 4.75; B, 2.08; N, 6.73.

[0125] Synthesis Example 5:

[0126] Synthesis of compound A-29

[0127]

[0128] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-29-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-29 (31% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 923.28; elemental analysis results: theoretical values: C, 81.91; H, 4.26; B, 2.34; N, 4.55; S, 6.94; experimental values: C, 81.91; H, 4.26; B, 2.34; N, 4.56; S, 6.94.

[0129] Synthesis Example 6:

[0130] Synthesis of compound A-35

[0131]

[0132] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-35-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-35 (31% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1019.17; elemental analysis results: theoretical values: C, 74.36; H, 3.86; B, 2.12; N, 4.13; Se, 15.52; experimental values: C, 74.36; H, 3.86; B, 2.13; N, 4.13; Se, 15.52.

[0133] Synthesis Example 7:

[0134] Synthesis of compound A-45

[0135]

[0136] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-45-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-45 (27% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 939.40; elemental analysis results: theoretical values: C, 80.51; H, 5.90; B, 2.30; N, 4.47; S, 6.82; experimental values: C, 80.51; H, 5.91; B, 2.30; N, 4.47; S, 6.82.

[0137] Synthesis Example 8:

[0138] Synthesis of compound A-51

[0139]

[0140] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-51-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-51 (26% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 939.49; elemental analysis results: theoretical values: C, 83.06; H, 6.76; B, 2.30; N, 4.47; S, 3.41; experimental values: C, 83.06; H, 6.76; B, 2.31; N, 4.47; S, 3.41.

[0141] Synthesis Example 9:

[0142] Synthesis of compound A-62

[0143]

[0144] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-62-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 25:1) to obtain the target compound A-62 (26% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 876.48; elemental analysis results: theoretical values: C, 83.56; H, 7.13; B, 2.47; N, 3.19; S, 3.66; experimental values: C, 83.56; H, 7.14; B, 2.47; N, 3.19; S, 3.66.

[0145] Synthesis Example 10:

[0146] Synthesis of compound A-67

[0147]

[0148] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-67-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-67 (31% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 982.35; elemental analysis results: theoretical values: C, 84.32; H, 4.51; B, 2.20; N, 5.70; S, 3.26; experimental values: C, 84.32; H, 4.51; B, 2.21; N, 5.70; S, 3.26.

[0149] Synthesis Example 11:

[0150] Synthesis of compound A-75

[0151]

[0152] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-75-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-75 (32% yield, HPLC purity 98%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 976.22; elemental analysis results: theoretical values: C, 70.24; H, 5.17; B, 2.22; N, 2.87; S, 3.29; Se, 16.20; experimental values: C, 70.25; H, 5.17; B, 2.22; N, 2.87; S, 3.29; Se, 16.21.

[0153] Synthesis Example 12:

[0154] Synthesis of compound A-100

[0155]

[0156] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-100-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-100 (33% yield, HPLC purity 98%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 862.43; elemental analysis results: theoretical values: C, 82.13; H, 6.54; B, 2.51; N, 3.25; O, 1.85; S, 3.72; experimental values: C, 82.12; H, 6.54; B, 2.51; N, 3.25; O, 1.85; S, 3.73.

[0157] Synthesis Example 13:

[0158] Synthesis of compound A-108

[0159]

[0160] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-108-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound A-108 (27% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1030.29; elemental analysis results: theoretical values: C, 80.48; H, 4.31; B, 2.10; N, 5.44; Se, 7.67; experimental values: C, 80.47; H, 4.31; B, 2.11; N, 5.44; Se, 7.67.

[0161] Synthesis Example 14:

[0162] Synthesis of compound A-123

[0163]

[0164] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-123-1 (3 mmol) at 0 °C, and the reaction was then carried out at 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-123 (29% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 966.43; elemental analysis results: theoretical values: C, 89.45; H, 5.42; B, 2.24; N, 2.90; experimental values: C, 89.46; H, 5.41; B, 2.24; N, 2.90.

[0165] Synthesis Example 15:

[0166] Synthesis of compound A-146

[0167]

[0168] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-146-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 30:1) to obtain the target compound A-146 (31% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1132.43; elemental analysis results: theoretical values: C, 85.86; H, 4.80; B, 1.91; N, 4.94; Si, 2.48; experimental values: C, 85.86; H, 4.81; B, 1.90; N, 4.94; Si, 2.48.

[0169] Synthesis Example 16:

[0170] Synthesis of compound A-153

[0171]

[0172] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-153-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-153 (29% yield, HPLC purity 98%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1073.36; elemental analysis results: theoretical values: C, 83.88; H, 4.60; B, 2.01; N, 3.91; S, 2.99; Si, 2.61; experimental values: C, 83.88; H, 4.61; B, 2.02; N, 3.91; S, 2.99; Si, 2.61.

[0173] Synthesis Example 17:

[0174] Synthesis of compound A-181

[0175]

[0176] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-181-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 25:1) to obtain the target compound A-181 (28% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 966.43; elemental analysis results: theoretical values: C, 89.45; H, 5.42; B, 2.24; N, 2.90; experimental values: C, 89.46; H, 5.42; B, 2.24; N, 2.91.

[0177] Synthesis Example 18:

[0178] Synthesis of compound A-186

[0179]

[0180] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-186-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-186 (30% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 940.38; elemental analysis results: theoretical values: C, 88.09; H, 4.93; B, 2.30; N, 2.98; O, 1.70; experimental values: C, 88.09; H, 4.93; B, 2.30; N, 2.99; O, 1.71.

[0181] Synthesis Example 19:

[0182] Synthesis of compound A-188

[0183]

[0184] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-188-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound A-188 (31% yield, HPLC purity 98%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 848.23; elemental analysis results: theoretical values: C, 80.67; H, 4.04; B, 2.55; N, 3.30; O, 1.89; S, 7.56; experimental values: C, 80.68; H, 4.04; B, 2.56; N, 3.30; O, 1.89; S, 7.56.

[0185] Synthesis Example 20:

[0186] Synthesis of compound A-195

[0187]

[0188] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor A-195-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-trimethylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 30:1) to obtain the target compound A-195 (31% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 806.28; elemental analysis results: theoretical values: C, 81.90; H, 4.50; B, 2.68; N, 6.95; S, 3.97; experimental values: C, 81.91; H, 4.52; B, 2.68; N, 6.95; S, 3.98.

[0189] Synthesis Example 21:

[0190] Synthesis of compound B-1

[0191]

[0192] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-1-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give intermediate B-1-2 as a yellow solid.

[0193] Under an oxygen atmosphere, intermediate B-1-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product B-1 (31% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 609.20; Elemental analysis results: Theoretical values: C, 84.74; H, 3.97; B, 1.77; N, 6.89; O, 2.62; Experimental values: C, 84.74; H, 3.97; B, 1.77; N, 6.88; O, 2.62.

[0194] Synthesis Example 22:

[0195] Synthesis of compound B-4

[0196]

[0197] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-4-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give intermediate B-4-2 as a yellow solid.

[0198] Under an oxygen atmosphere, intermediate B-4-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 30:1) to obtain the target product B-4 (30% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 833.45; Elemental analysis results: Theoretical values: C, 84.98; H, 6.77; B, 1.30; N, 5.04; O, 1.92; Experimental values: C, 84.98; H, 6.77; B, 1.31; N, 5.06; O, 1.91.

[0199] Synthesis Example 23:

[0200] Synthesis of compound B-7

[0201]

[0202] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-7-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-7-2, which was a yellow solid.

[0203] Under an oxygen atmosphere, intermediate B-7-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-7 (29% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 939.32; Elemental analysis results: Theoretical values: C, 85.62; H, 4.08; B, 1.15; N, 7.45; O, 1.70; Experimental values: C, 85.62; H, 4.08; B, 1.15; N, 7.45; O, 1.71.

[0204] Synthesis Example 24:

[0205] Synthesis of compound B-19

[0206]

[0207] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-19-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-19-2, which was a yellow solid.

[0208] Under an oxygen atmosphere, intermediate B-19-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give the target product B-19 (31% yield, 98% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 939.32; Elemental analysis results: Theoretical values: C, 85.62; H, 4.08; B, 1.15; N, 7.45; O, 1.70; Experimental values: C, 85.62; H, 4.07; B, 1.16; N, 7.45; O, 1.71.

[0209] Synthesis Example 25:

[0210] Synthesis of compound B-29

[0211]

[0212] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-29-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-29-2, which was a yellow solid.

[0213] Under an oxygen atmosphere, intermediate B-29-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give the target product B-29 (29% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.18; Elemental analysis results: Theoretical values: C, 80.39; H, 3.43; B, 1.32; N, 5.11; O, 1.95; S, 7.80; Experimental values: C, 80.39; H, 3.43; B, 1.31; N, 5.11; O, 1.95; S, 7.80.

[0214] Synthesis Example 26:

[0215] Synthesis of compound B-35

[0216]

[0217] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-35-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain intermediate B-35-2, which was a yellow solid.

[0218] Under an oxygen atmosphere, intermediate B-35-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 30:1) to obtain the target product B-35 (29% yield, HPLC purity 98%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 917.07; Elemental analysis results: Theoretical values: C, 72.15; H, 3.08; B, 1.18; N, 4.59; O, 1.75; Se, 17.25; Experimental values: C, 72.16; H, 3.08; B, 1.18; N, 4.59; O, 1.75; Se, 17.25.

[0219] Synthesis Example 27:

[0220] Synthesis of compound B-45

[0221]

[0222] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-45-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give intermediate B-45-2 as a yellow solid.

[0223] Under an oxygen atmosphere, intermediate B-45-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-45 (33% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 837.30; Elemental analysis results: Theoretical values: C, 78.84; H, 5.29; B, 1.29; N, 5.01; O, 1.91; S, 7.65; Experimental values: C, 78.84; H, 5.29; B, 1.28; N, 5.02; O, 1.91; S, 7.65.

[0224] Synthesis Example 28:

[0225] Synthesis of compound B-51

[0226]

[0227] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-51-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain intermediate B-51-2, which was a yellow solid.

[0228] Under an oxygen atmosphere, intermediate B-51-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product B-51 (29% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 837.39; Elemental analysis results: Theoretical values: C, 81.70; H, 6.26; B, 1.29; N, 5.01; O, 1.91; S, 3.83; Experimental values: C, 81.71; H, 6.27; B, 1.29; N, 5.01; O, 1.91; S, 3.83.

[0229] Synthesis Example 29:

[0230] Synthesis of compound B-62

[0231]

[0232] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-62-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-62-2 as a yellow solid.

[0233] Under an oxygen atmosphere, intermediate B-62-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product B-62 (24% yield, 98% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 774.38; Elemental analysis results: Theoretical values: C, 82.15; H, 6.63; B, 1.40; N, 3.62; O, 2.06; S, 4.14; Experimental values: C, 82.15; H, 6.63; B, 1.41; N, 3.62; O, 2.06; S, 4.14.

[0234] Synthesis Example 30:

[0235] Synthesis of compound B-67

[0236]

[0237] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-67-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain intermediate B-67-2, which was a yellow solid.

[0238] Under an oxygen atmosphere, intermediate B-67-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 30:1) to obtain the target product B-67 (25% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 880.25; Elemental analysis results: Theoretical values: C, 83.18; H, 3.78; B, 1.23; N, 6.36; O, 1.82; S, 3.64; Experimental values: C, 83.18; H, 3.78; B, 1.22; N, 6.37; O, 1.82; S, 3.64.

[0239] Synthesis Example 31:

[0240] Synthesis of compound B-75

[0241]

[0242] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-75-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-75-2, which was a yellow solid.

[0243] Under an oxygen atmosphere, intermediate B-75-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-75 (29% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 874.12; Elemental analysis results: Theoretical values: C, 67.44; H, 4.50; B, 1.24; N, 3.21; O, 1.83; S, 3.67; Se, 18.10; Experimental values: C, 67.44; H, 4.50; B, 1.24; N, 3.22; O, 1.83; S, 3.68; Se, 18.10.

[0244] Synthesis Example 32:

[0245] Synthesis of compound B-100

[0246]

[0247] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-100-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain intermediate B-100-2, which was a yellow solid.

[0248] Under an oxygen atmosphere, intermediate B-100-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product B-100 (31% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 760.33; Elemental analysis results: Theoretical values: C, 80.52; H, 5.96; B, 1.42; N, 3.68; O, 4.21; S, 4.21; Experimental values: C, 80.52; H, 5.97; B, 1.42; N, 3.68; O, 4.21; S, 4.21.

[0249] Synthesis Example 33:

[0250] Synthesis of compound B-108

[0251]

[0252] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-108-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-108-2, which was a yellow solid.

[0253] Under an oxygen atmosphere, intermediate B-108-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-108 (29% yield, 99% HPLC purity) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 928.19; Elemental analysis results: Theoretical values: C, 78.97; H, 3.59; B, 1.17; N, 6.04; O, 1.72; Se, 8.51; Experimental values: C, 78.98; H, 3.59; B, 1.17; N, 6.05; O, 1.72; Se, 8.51.

[0254] Synthesis Example 34:

[0255] Synthesis of compound B-123

[0256]

[0257] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-123-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain intermediate B-123-2 as a yellow solid.

[0258] Under an oxygen atmosphere, intermediate B-123-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 30:1) to obtain the target product B-123 (31% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 864.33; Elemental analysis results: Theoretical values: C, 88.88; H, 4.78; B, 1.25; N, 3.24; O, 1.85; Experimental values: C, 88.88; H, 4.78; B, 1.25; N, 3.25; O, 1.86.

[0259] Synthesis Example 35:

[0260] Synthesis of compound B-146

[0261]

[0262] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-146-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-146-2, which was a yellow solid.

[0263] Under an oxygen atmosphere, intermediate B-146-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-146 (29% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1030.33; Elemental analysis results: Theoretical values: C, 85.04; H, 4.20; B, 1.05; N, 5.43; O, 1.55; Si, 2.72; Experimental values: C, 85.03; H, 4.20; B, 1.05; N, 5.43; O, 1.55; Si, 2.71.

[0264] Synthesis Example 36:

[0265] Synthesis of compound B-153

[0266]

[0267] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-153-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-153-2, which was a yellow solid.

[0268] Under an oxygen atmosphere, intermediate B-153-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-153 (25% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 971.26; Elemental analysis results: Theoretical values: C, 82.79; H, 3.94; B, 1.11; N, 4.32; O, 1.65; S, 3.30; Si, 2.89; Experimental values: C, 82.78; H, 3.95; B, 1.11; N, 4.32; O, 1.65; S, 3.30; Si, 2.89.

[0269] Synthesis Example 37:

[0270] Synthesis of compound B-181

[0271]

[0272] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-181-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain intermediate B-181-2, which was a yellow solid.

[0273] Under an oxygen atmosphere, intermediate B-181-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain the target product B-181 (22% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 864.33; Elemental analysis results: Theoretical values: C, 88.88; H, 4.78; B, 1.25; N, 3.24; O, 1.85; Experimental values: C, 88.88; H, 4.78; B, 1.26; N, 3.24; O, 1.86.

[0274] Synthesis Example 38:

[0275] Synthesis of compound B-186

[0276]

[0277] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-186-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-186-2, which was a yellow solid.

[0278] Under an oxygen atmosphere, intermediate B-186-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-186 (32% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 838.28; Elemental analysis results: Theoretical values: C, 87.35; H, 4.21; B, 1.29; N, 3.34; O, 3.81; Experimental values: C, 87.35; H, 4.21; B, 1.29; N, 3.33; O, 3.81.

[0279] Synthesis Example 39:

[0280] Synthesis of compound B-188

[0281]

[0282] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-188-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain intermediate B-188-2, which was a yellow solid.

[0283] Under an oxygen atmosphere, intermediate B-188-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 30:1) to obtain the target product B-188 (23% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 746.13; Elemental analysis results: Theoretical values: C, 78.82; H, 3.11; B, 1.45; N, 3.75; O, 4.29; S, 8.59; Experimental values: C, 78.82; H, 3.11; B, 1.46; N, 3.76; O, 4.29; S, 8.59.

[0284] Synthesis Example 40:

[0285] Synthesis of compound B-195

[0286]

[0287] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor B-195-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate B-195-2, which was a yellow solid.

[0288] Under an oxygen atmosphere, intermediate B-195-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product B-195 (29% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 704.18; Elemental analysis results: Theoretical values: C, 80.12; H, 3.58; B, 1.53; N, 7.95; O, 2.27; S, 4.55; Experimental values: C, 80.11; H, 3.58; B, 1.53; N, 7.95; O, 2.27; S, 4.55.

[0289] Synthesis Example 41:

[0290] Synthesis of compound C-4

[0291]

[0292] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-4-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 30:1) to obtain the target product C-4 (30% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 969.52; Elemental analysis results: Theoretical values: C, 87.90; H, 6.65; B, 1.11; N, 4.33; Experimental values: C, 87.91; H, 6.66; B, 1.11; N, 4.33.

[0293] Synthesis Example 42:

[0294] Synthesis of compound C-10

[0295]

[0296] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-10-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product C-10 (28% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1075.38; Elemental analysis results: Theoretical values: C, 88.18; H, 4.31; B, 1.00; N, 6.51; Experimental values: C, 88.17; H, 4.31; B, 1.01; N, 6.51.

[0297] Synthesis Example 43:

[0298] Synthesis of compound C-22

[0299]

[0300] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-22-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain the target product C-22 (29% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1016.31; Elemental analysis results: Theoretical values: C, 86.21; H, 4.06; B, 1.06; N, 5.51; S, 3.15; Experimental values: C, 86.21; H, 4.06; B, 1.07; N, 5.51; S, 3.15.

[0301] Synthesis Example 44:

[0302] Synthesis of compound C-28

[0303]

[0304] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-28-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours at each temperature. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product C-28 (29% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 957.48; Elemental analysis results: Theoretical values: C, 86.50; H, 6.31; B, 1.13; N, 4.39; O, 1.67; Experimental values: C, 86.51; H, 6.31; B, 1.13; N, 4.39; O, 1.68.

[0305] Synthesis Example 45:

[0306] Synthesis of compound C-35

[0307]

[0308] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-35-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain the target product C-35 (25% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1016.31; Elemental analysis results: Theoretical values: C, 86.21; H, 4.06; B, 1.06; N, 5.51; S, 3.15; Experimental values: C, 86.22; H, 4.05; B, 1.06; N, 5.51; S, 3.15.

[0309] Synthesis Example 46:

[0310] Synthesis of compound C-48

[0311]

[0312] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-48-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain the target product C-48 (29% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 941.27; Elemental analysis results: Theoretical values: C, 85.44; H, 3.85; B, 1.15; N, 4.46; O, 1.70; S, 3.40; Experimental values: C, 85.44; H, 3.85; B, 1.16; N, 4.47; O, 1.70; S, 3.39.

[0313] Synthesis Example 47:

[0314] Synthesis of compound C-60

[0315]

[0316] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-60-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours at each temperature. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain the target product C-60 (31% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 962.24; Elemental analysis results: Theoretical values: C, 76.16; H, 4.92; B, 1.12; N, 2.91; S, 6.67; Se, 8.21; Experimental values: C, 76.17; H, 4.92; B, 1.12; N, 2.90; S, 6.67; Se, 8.21.

[0317] Synthesis Example 48:

[0318] Synthesis of compound C-83

[0319]

[0320] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-83-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours at each temperature. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product C-83 (29% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 890.29; Elemental analysis results: Theoretical values: C, 87.63; H, 4.41; B, 1.21; N, 3.14; S, 3.60; Experimental values: C, 87.65; H, 4.41; B, 1.20; N, 3.14; S, 3.61.

[0321] Synthesis Example 49:

[0322] Synthesis of compound C-93

[0323]

[0324] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-93-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours at each temperature. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product C-93 (28% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 850.33; Elemental analysis results: Theoretical values: C, 87.52; H, 4.62; B, 1.27; N, 6.59; Experimental values: C, 87.51; H, 4.61; B, 1.27; N, 6.59.

[0325] Synthesis Example 50:

[0326] Synthesis of compound C-99

[0327]

[0328] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-99-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain the target product C-99 (29% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 990.32; Elemental analysis results: Theoretical values: C, 88.47; H, 4.37; B, 1.09; N, 2.83; S, 3.24; Experimental values: C, 88.47; H, 4.36; B, 1.09; N, 2.83; S, 3.24.

[0329] Synthesis Example 51:

[0330] Synthesis of compound C-118

[0331]

[0332] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-118-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product C-118 (26% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 809.21; Elemental analysis results: Theoretical values: C, 81.58; H, 3.98; B, 1.33; N, 5.19; S, 7.92; Experimental values: C, 81.58; H, 3.98; B, 1.33; N, 5.18; S, 7.91.

[0333] Synthesis Example 52:

[0334] Synthesis of compound C-125

[0335]

[0336] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-125-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product C-125 (24% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1125.40; Elemental analysis results: Theoretical values: C, 88.52; H, 4.30; B, 0.96; N, 6.22; Experimental values: C, 88.52; H, 4.30; B, 0.96; N, 6.23.

[0337] Synthesis Example 53:

[0338] Synthesis of compound C-139

[0339]

[0340] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-139-1 (3 mmol) at 0 °C, and the mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-triisopropylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 15:1) to obtain the target compound C-139 (28% yield, HPLC purity 98%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1066.44; elemental analysis results: theoretical values: C, 84.43; H, 5.29; B, 2.03; N, 5.25; S, 3.00; experimental values: C, 84.43; H, 5.30; B, 2.03; N, 5.25; S, 3.01.

[0341] Synthesis Example 54:

[0342] Synthesis of compound C-149

[0343]

[0344] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-149-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was then added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature, and the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to obtain intermediate C-149-2, which was a yellow solid.

[0345] Under an oxygen atmosphere, intermediate C-149-2 (1 mmol) was dissolved in 100 mL of DMSO. 2,3-Dichloro-5,6-dicyanobenzoquinone (36 mmol) was slowly added to the reaction flask at room temperature. Finally, the mixture was reacted at room temperature for 72 h. The reaction mixture was carefully quenched with H₂O and MeOH, and the pH of the solution was adjusted to 7.0 with phosphate buffer. The mixture was then extracted three times with DCM, the organic layer was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to obtain the target product C-149 (31% yield, 99% purity according to HPLC analysis) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 931.32; Elemental analysis results: Theoretical values: C, 86.36; H, 4.22; B, 1.16; F, 2.04; N, 4.51; O, 1.72; Experimental values: C, 86.36; H, 4.23; B, 1.16; F, 2.04; N, 4.51; O, 1.73.

[0346] Synthesis Example 55:

[0347] Synthesis of compound C-155

[0348]

[0349] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 6.6 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-155-1 (3 mmol) at 0 °C. The mixture was then heated to 60 °C for 3 hours each time. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (7.5 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (15 mmol) was added at room temperature, and the reaction was continued at 145 °C for 5 hours. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 20:1) to obtain the target product C-155 (22% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1117.38; Elemental analysis results: Theoretical values: C, 85.94; H, 4.24; B, 0.97; F, 5.10; N, 3.76; Experimental values: C, 85.94; H, 4.24; B, 0.97; F, 5.10; N, 3.78.

[0350] Synthesis Example 56:

[0351] Synthesis of compound C-162

[0352]

[0353] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (1.60 M, 12 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of the brominated precursor C-162-1 (3 mmol) at 0 °C, and the reaction was then carried out at 60 °C for 3 hours each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (12 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours, then heated to 60 °C and stirred for 2 hours. N,N-diisopropylethylamine (24 mmol) was added at room temperature, and the reaction was continued at 145 °C for 12 hours. Then, a tetrahydrofuran solution of 2,4,6-triisopropylphenyl magnesium bromide (1.0 M, 12 mmol) was added at room temperature, and the reaction was stopped after 6 hours. After the reaction was complete, the solvent was removed by rotary evaporation. The crude product was purified by silica gel column chromatography (electrolyte: petroleum ether: dichloromethane = 20:1) to obtain the target compound C-162 (29% yield, HPLC purity 99%), as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1024.33; elemental analysis results: theoretical values: C, 80.86; H, 4.92; B, 2.11; N, 2.73; S, 9.38; experimental values: C, 80.86; H, 4.92; B, 2.11; N, 2.71; S, 9.38.

[0354] The photophysical properties of the representative fused-ring compounds prepared in the above-described synthetic examples of the present invention are shown in Table 1.

[0355] Table 1:

[0356]

[0357]

[0358]

[0359] Note: In Table 1, quantum efficiency is the ratio of the average number of photoelectrons generated per unit time to the number of incident photons at a specific wavelength. This is calculated by using compounds with a quantum efficiency of 10... -5 The sample was prepared by dissolving the compound in toluene at a concentration of mol / L, and then measured after deoxygenation under nitrogen. The instrument was an Edinburgh FLS1000 (UK). The half-width at half-maximum (WHM) is the width of the peak at half the peak height of the fluorescence spectrum at room temperature. It is calculated by drawing a straight line parallel to the base of the peak through the midpoint of the peak height, and finding the distance between the two points where this line intersects the peak. The fluorescence spectrum is obtained by measuring the compound at 10 mol / L concentrations. -5 The sample was prepared by dissolving it in toluene at a concentration of mol / L and then tested using a fluorescence spectrometer (Edinburg FLS1000 (UK)).

[0360] As can be seen from Table 1, the fused ring compounds in the embodiments provided by the present invention have high quantum efficiency (>85%), while the luminescent compounds provided by the present invention exhibit narrow half-width (<20nm).

[0361] The technical effects and advantages of the present invention will be demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices and testing their actual performance.

[0362] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0363] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0364] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0365] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0366] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include sensitizers and host materials. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0367] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0368] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0369] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0370] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~8×10 -4 Pa, a hole injection layer is formed by vacuum evaporation of hole injection material on the above-mentioned anolyte film, with an evaporation rate of 0.1-0.5 nm / s;

[0371] 3. A hole transport layer is formed by vacuum evaporation of hole transport material on top of the hole injection layer, with an evaporation rate of 0.1-0.5 nm / s;

[0372] 4. An organic light-emitting layer of the device is vacuum-deposited on top of the hole transport layer. The organic light-emitting layer material includes a host material, a sensitizer, and a dye. The evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted by using a multi-source co-evaporation method to make the dye reach a preset doping ratio.

[0373] 5. An electron transport layer is formed by vacuum evaporating the electron transport material of the device on top of the organic light-emitting layer, with an evaporation rate of 0.1-0.5 nm / s;

[0374] 6. On the electron transport layer, LiF is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer, and Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0375] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0376] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0377] Device Example 1

[0378] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0379] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0380] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-1 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0381] Device Example 2

[0382] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-4 instead of A-1. The device structure is as follows:

[0383] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0384] Device Example 3

[0385] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-7 instead of A-1. The device structure is as follows:

[0386] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-7(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0387] Device Example 4

[0388] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-19 instead of A-11. The device structure is as follows:

[0389] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-19(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0390] Device Example 5

[0391] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-29 instead of A-1. The device structure is as follows:

[0392] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-29(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0393] Device Example 6

[0394] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-35 instead of A-1. The device structure is as follows:

[0395] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-35(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0396] Device Example 7

[0397] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-45 instead of A-1. The device structure is as follows:

[0398] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-45(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0399] Device Example 8

[0400] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-51 instead of A-1. The device structure is as follows:

[0401] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-51(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0402] Device Example 9

[0403] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-62 instead of A-1. The device structure is as follows:

[0404] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-62(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0405] Device Example 10

[0406] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with A-67 instead of A-1. The device structure is as follows:

[0407] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-67(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0408] Device Example 11

[0409] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-75 instead of A-1. The device structure is as follows:

[0410] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-75(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0411] Device Example 12

[0412] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with A-100 instead of A-1. The device structure is as follows:

[0413] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-100(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0414] Device Example 13

[0415] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-108 instead of A-1. The device structure is as follows:

[0416] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-108(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0417] Device Example 14

[0418] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-123 instead of A-1. The device structure is as follows:

[0419] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-123(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0420] Device Example 15

[0421] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-146 instead of A-1. The device structure is as follows:

[0422] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-146(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0423] Device Example 16

[0424] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-153 instead of A-1. The device structure is as follows:

[0425] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-153(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0426] Device Example 17

[0427] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-181 instead of A-1. The device structure is as follows:

[0428] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-181(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0429] Device Example 18

[0430] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with A-186 instead of A-1. The device structure is as follows:

[0431] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-186(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0432] Device Example 19

[0433] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-188 instead of A-1. The device structure is as follows:

[0434] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-188(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0435] Device Example 20

[0436] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with A-195 instead of A-1. The device structure is as follows:

[0437] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-195(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0438] Device Example 21

[0439] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with B-1 instead of A-1. The device structure is as follows:

[0440] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0441] Device Example 22

[0442] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-4 instead of A-1. The device structure is as follows:

[0443] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0444] Device Example 23

[0445] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with B-7 instead of A-1. The device structure is as follows:

[0446] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-7(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0447] Device Example 24

[0448] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-19 instead of A-1. The device structure is as follows:

[0449] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-19(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0450] Device Example 25

[0451] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-29 instead of A-1. The device structure is as follows:

[0452] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-29(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0453] Device Example 26

[0454] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-35 instead of A-1. The device structure is as follows:

[0455] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-35(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0456] Device Example 27

[0457] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-45 instead of A-1. The device structure is as follows:

[0458] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-45(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0459] Device Example 28

[0460] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-51 instead of A-1. The device structure is as follows:

[0461] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-51(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0462] Device Example 29

[0463] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-62 instead of A-1. The device structure is as follows:

[0464] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-62(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0465] Device Example 30

[0466] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-67 instead of A-1. The device structure is as follows:

[0467] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-67(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0468] Device Example 31

[0469] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-75 instead of A-1. The device structure is as follows:

[0470] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-75(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0471] Device Example 32

[0472] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-100 instead of A-1. The device structure is as follows:

[0473] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-100(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0474] Device Example 33

[0475] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-108 instead of A-1. The device structure is as follows:

[0476] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-108(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0477] Device Example 34

[0478] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-123 instead of A-1. The device structure is as follows:

[0479] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-123(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0480] Device Example 35

[0481] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with B-146 instead of A-1. The device structure is as follows:

[0482] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-146(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0483] Device Example 36

[0484] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-153 instead of A-1. The device structure is as follows:

[0485] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-153(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0486] Device Example 37

[0487] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-181 instead of A-1. The device structure is as follows:

[0488] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-181(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0489] Device Example 38

[0490] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with B-186 instead of A-1. The device structure is as follows:

[0491] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-186(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0492] Device Example 39

[0493] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-188 instead of A-1. The device structure is as follows:

[0494] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-188(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0495] Device Example 40

[0496] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with B-195 instead of A-1. The device structure is as follows:

[0497] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-195(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0498] Device Example 41

[0499] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-4 instead of A-1. The device structure is as follows:

[0500] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0501] Device Example 42

[0502] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-10 instead of A-1. The device structure is as follows:

[0503] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-10(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0504] Device Example 43

[0505] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with C-22 instead of A-1. The device structure is as follows:

[0506] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-22(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0507] Device Example 44

[0508] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-28 instead of A-1. The device structure is as follows:

[0509] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-28(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0510] Device Example 45

[0511] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-35 instead of A-1. The device structure is as follows:

[0512] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-35(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0513] Device Example 46

[0514] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-48 instead of A-1. The device structure is as follows:

[0515] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-48(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0516] Device Example 47

[0517] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-60 instead of A-1. The device structure is as follows:

[0518] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-60(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0519] Device Example 48

[0520] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-83 instead of A-1. The device structure is as follows:

[0521] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-83(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0522] Device Example 49

[0523] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with C-93 instead of A-1. The device structure is as follows:

[0524] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-93(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0525] Device Example 50

[0526] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-99 instead of A-1. The device structure is as follows:

[0527] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-99(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0528] Device Example 51

[0529] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-118 instead of A-1. The device structure is as follows:

[0530] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-118(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0531] Device Example 52

[0532] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-125 instead of A-1. The device structure is as follows:

[0533] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-125(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0534] Device Example 53

[0535] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-139 instead of A-1. The device structure is as follows:

[0536] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-139(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0537] Device Example 54

[0538] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-149 instead of A-1. The device structure is as follows:

[0539] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-149(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0540] Device Example 55

[0541] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-155 instead of A-1. The device structure is as follows:

[0542] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-155(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0543] Device Example 56

[0544] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with C-162 instead of A-1. The device structure is as follows:

[0545] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-162(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0546] Comparative Device Example 1

[0547] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with D1 instead of A-1. The device structure is as follows:

[0548] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%D1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0549] Comparative Device Example 2

[0550] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with D2 instead of A-1. The device structure is as follows:

[0551] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%D2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0552] Comparative Device Example 3

[0553] The fabrication method is the same as that in Device Example 1, except that the dye used in the light-emitting layer is replaced with D3 instead of A-1. The device structure is as follows:

[0554] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%D3(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0555] Comparative Device Example 4

[0556] The fabrication method is the same as that of Device Example 1, except that the dye used in the light-emitting layer is replaced with D4 instead of A-1. The device structure is as follows:

[0557] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%D4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0558] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0559]

[0560]

[0561] The aforementioned comparative compounds D1-D4 are compounds in the prior art, and their synthesis methods can be found in patent applications CN 112679534, CN 114106022, CN 113540371, CN107851724, etc., which will not be repeated here.

[0562] The performance of the organic electroluminescent devices prepared in the above embodiments and comparative examples is shown in Table 2 below.

[0563] Table 2:

[0564]

[0565]

[0566]

[0567]

[0568] In Comparative Example 1, the structure also involves a six-membered ring superimposed below the central benzene ring to increase the conjugation of the molecule. However, the nitrogen atom is located at the para position of boron, which is an electron-donating group that can increase the emission band gap of the molecule, thereby causing a blue shift in the light color and resulting in a blue light material. In contrast, in the material we designed, the methyl boron or carbonyl group is a strong electron-withdrawing group that can significantly reduce the LUMO energy level, thereby reducing the emission band gap of the molecule and causing a red shift in the light color, resulting in narrow-spectral emission of green or even orange-red light, which greatly broadens the light color range of the material. In Comparative Example 2, its structure is similar to the structure of the boron para-substituted or unsubstituted fluorenyl group we designed. However, due to the relatively small size of the two methyl groups, the molecular structure is relatively flat, resulting in strong intermolecular interactions. This leads to concentration quenching, which significantly reduces luminous efficiency and stability. In contrast, the twisted structure of the fluorenyl group can effectively reduce intermolecular interactions, thereby reducing problems such as redshift, broadening, and efficiency reduction caused by molecular stacking. It significantly suppresses the concentration quenching effect, improves the stability and reproducibility of the device, and can also increase the doping concentration to reduce the fabrication difficulty of the device, which is conducive to the commercial application of the material. In Comparative Example 3, an additional six-membered ring was added to the six-membered structure to broaden the conjugation of the molecule. The B-π-B, N-π-N structure significantly reduced the emission band gap, resulting in a red-light molecule. However, its relatively flat structure led to significant molecular packing, causing a noticeable broadening of the spectrum. In contrast, our designed molecule only introduces a six-membered ring below the central benzene ring, achieving a red shift while maintaining structural rigidity and distortion, thus achieving efficient, stable, and pure green light emission. Comparative Example 4 uses a nitrogen-boron-nitrogen multiple resonance material core with carbazole as the donor group and no other surrounding groups. Compared to the structure designed in this invention, which incorporates a six-membered ring below the central benzene ring in the core structure, its structural rigidity and stability are relatively weak, and the excited-state structure has a greater degree of relaxation, resulting in an increased full width at half maximum (FWHM), reduced color purity, and poorer device lifetime. The device prepared using the molecule of this invention has higher efficiency, longer lifetime, and can achieve a red shift in the spectrum, producing narrow-spectrum green or even orange-red light.

[0569] The experimental data above show that, compared to Comparative Examples 1-4, devices using the compounds of this invention in Examples 1-56, with the same materials for other functional layers in the organic electroluminescent device structure, exhibit narrower electroluminescence spectra. Furthermore, compared to the multiple resonance TADF dyes with similar structures in the comparative examples, devices prepared with the compounds provided by this invention have higher external quantum efficiency and longer lifetimes. Moreover, they can achieve a redshift in the spectrum, yielding narrow-spectrum green and even orange-red light materials.

[0570] The reason for this is that the compounds of this invention increase the degree of molecular conjugation by introducing a six-membered ring below the central benzene ring in the parent structure. On the one hand, introducing a six-membered ring increases the degree of molecular conjugation, reduces the emission band gap, thereby causing a red shift in light color. Furthermore, by changing the electron-withdrawing and electron-donating abilities of X and Y on the six-membered ring, the emission color can be broadly adjusted, achieving a relatively wide color gamut coverage. On the other hand, increasing the degree of molecular conjugation through a six-membered ring also significantly improves the structural rigidity of the molecule, thereby reducing the relaxation degree of the excited state structure and improving the luminescence efficiency, color purity, and stability of the molecule.

[0571] When X is an electron-withdrawing group, such as microboron or carbonyl, it can lower the LUMO energy level, significantly reducing the emission band gap and redshifting the emission, thereby achieving narrow-spectrum green or even orange-red light emission. Furthermore, when X is microboron or fluorene, its distorted structure can effectively reduce intermolecular interactions, thereby reducing problems such as redshift, broadening, and efficiency reduction caused by molecular stacking. It can also significantly suppress concentration quenching effects, improve device stability and reproducibility, and increase doping concentration, thereby reducing the difficulty of device fabrication and facilitating the commercial application of the material.

[0572] When Y is an electron-donating group such as O, S, or Se, it can increase the HOMO energy level, thereby reducing the emission band gap and resulting in a redshift in emission. Furthermore, S and Se are heavy atoms, which can promote spin-orbit coupling through the heavy atom effect, thus facilitating the upconversion of triplet excitons and improving luminescence efficiency and device stability. However, when Y is an NR... 12 CR 13 R 14 or SiR 15 R 16 When electron-donating groups are used, not only can the light color be red-shifted, but the R group can also be a sterically hindered group, which can effectively reduce intermolecular interactions. This reduces problems such as red-shift, broadening, and efficiency reduction caused by molecular stacking, significantly suppresses concentration quenching effect, improves device stability and repeatability, and can also increase doping concentration to reduce the difficulty of device fabrication, which is conducive to the commercial application of materials.

[0573] The full width at half maximum (FWHM) of the electroluminescence spectrum of the device prepared in the examples shows that it has an effective multiple resonance effect, which greatly enriches the material system and emission color range of multiple resonance-thermally activated delayed fluorescence and has good application prospects.

[0574] The experimental data above show that the organic material of the present invention, as the light-emitting object of organic electroluminescent devices, is a high-performance organic light-emitting functional material and is expected to be promoted for commercial application.

[0575] Although the invention has been described in conjunction with embodiments, the invention is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention.

[0576] Obviously, the above embodiments are merely examples for clear illustration and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description, and any obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound having a structure as shown in formula (1), formula (2) or formula (3): Equation (1) Equation (2) （3） in: Cycles Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently selected from aromatic rings of C6 to C30 or heteroaromatic rings of C3 to C30; W1 and W2 are independently either CC single bonds or NR7; m1 and m2 are independently either 0 or 1. W3 and W4 are each independently selected from N or C; Y is selected from O, S, Se, NR 12 , CR 13 R 14 or SiR 15 R 16 ; X is selected from BAr6(R6) n6 or C=O, or X is selected from fluorenyl; The ring Ar6 is selected from an aromatic ring of C6 to C60, and R6 is selected from a chain alkyl group of C1 to C30; R1, R2, R3, R4, and R5 are each independently selected from one of the following groups: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, furanyl, benzofuranyl, thiopheneyl, benzothiopheneyl, pyrroleyl, isoindolyl, carbazoyl, indoxarcarbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indoxaryl, imidazoleyl, benzimidazolyl-1,2-thiazoyl, 1,3-thiazoyl, benzothiazoyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and 1,3,5-triazinyl, or a combination of the above two groups. n1, n2, n3, n4, n5, and n6 are each independently selected from integers from 1 to 5; When n1, n2, n3, n4, n5, and n6 are each independent integers greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, multiple R4s, multiple R5s, and multiple R6s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, the multiple R4s are either not connected or connected in a cycle, the multiple R5s are either not connected or connected in a cycle, and the multiple R6s are either not connected or connected in a cycle. R7, R 12 R 13 R 14 R 15 and R 16 Each group is independently selected from one of the following groups: C1~C36 chain alkyl, C6~C60 aryl; R 13 With R 14 If they are not connected or are connected in a loop, R 15 With R 16 They are either not connected or connected in a loop; And R 12 R 13 R 14 R 15 R 16 Each of them is independent and either not connected to rings Ar2 and Ar5, or connected to form a ring. 12 R 13 R 14 R 15 R 16 Each of them is independent and either not connected to R2 or R5, or connected to form a loop; Furthermore, each R6 is independently unconnected to ring Ar4 or ring Ar5, or connected to form a ring; each R6 is independently unconnected to R4 or R5, or connected to form a ring. Not selected from the following compounds: 。 2. The organic compound according to claim 1, characterized in that, The rings Ar1, Ar2, Ar3, and Ar4 each independently have the structure shown in formula (a) or formula (b), and the double bonds in the dashed lines represent the fusion positions of the groups: In equation (a), Z 1 Z 2 Z 3 Z 4 Each is independently selected from C, CH, or N; In equation (b), Z 5 Selected from O or S; The ring H is selected from C6-C30 aromatic rings.

3. The organic compound according to claim 2, characterized in that, Ring H is a benzene ring; Z 5 Selected from S.

4. The organic compound according to claim 2, characterized in that, One of the rings Ar1, Ar2, Ar3, and Ar4 is the structure shown in equation (b), and the other ring structures are each independently the structure shown in equation (a).

5. The organic compound according to claim 1, wherein each of the rings Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 is independently selected from one of a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a furan or a thiophene.

6. The organic compound according to claim 1, wherein each of the rings Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 is independently a benzene ring.

7. The organic compound according to claim 1, characterized in that, In equation (1), W1 and W2 are CC single bonds; m1 and m2 are 1; in equation (2), W1 is a CC single bond; m1 and m2 are 1.

8. The organic compound according to any one of claims 1, 2, or 5, characterized in that, X is BAr6 (R6) n6 When Y is selected from O, S, NR 12 ; When X is C=O, Y is selected from O, S, and NR. 12 ; When X is a fluorene group, Y is selected from O, S, and NR. 12 .

9. The organic compound according to claim 1, characterized in that, R1, R2, R3, R4, and R5 are each independently selected from one of the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, carbazole, and 1,3,5-triazinyl, or a combination of two of the above groups; R6 is selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

10. The organic compound according to claim 1, characterized in that, The R7, R 12 R 13 R 14 R 15 R 16 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl.

11. A compound selected from compounds with the following specific structures: 。 12. The application of the compound according to any one of claims 1-11, wherein the application is as a functional material in an organic electronic device, the organic electronic device being selected from organic electroluminescent devices, optical sensors, organic thin-film transistors, and organic field-effect transistors; The compound is used as a luminescent material in the luminescent layer of an organic electroluminescent device.

13. An organic electroluminescent device, comprising a first electrode layer, a second electrode layer, and one or more light-emitting functional layers inserted between the first electrode layer and the second electrode layer, wherein the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is formed on the first electrode layer, the second electrode layer is formed on the electron transport region, and the light-emitting layer is located between the hole transport region and the electron transport region; wherein... The light-emitting layer contains any of the compounds described in claims 1-11.

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